


Playing Catch Up

by allofthepixels



Series: Bestest 'Verse [3]
Category: Supernatural
Genre: Babysitter Castiel, Bestest 'Verse, Blow Jobs, Handcuffs, Lifeguard Dean, M/M, Teasing, Tickling, post-orgasm tickling, wee!archangels
Language: English
Status: Completed
Published: 2015-02-04
Updated: 2015-02-04
Packaged: 2018-03-10 11:13:10
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,982
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3288212
Author URL: https://archiveofourown.org/users/allofthepixels/pseuds/allofthepixels
Summary: <blockquote class="userstuff">
              <p>Dean realizes Cas has been holding out on him.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> These two are cute and I am trash.

Cas checked his phone for what might’ve been the fifth time in the last hour. Thursdays were the best chance to spend quality alone time with one another during their working hours. Cas liked Thursdays best, he decided.

He knew Dean’s break started at 1:30 exactly and his cousin’s swim lessons with Jo fell perfectly in that time-frame; it gave the most time for the two to grab some lunch, hang out, maybe fool around. Cas smiled to himself at the last part. Hopefully. He waited by their usual spot, a cluster of unused chairs and tables behind the Lifeguard’s equipment shack that offered enough privacy while still being within earshot of the pool. 

"Cas? You still here?" Dean appeared, having shed his tank top at some point during the last fifteen minutes of his shift. His eyes softened when they landed on Cas, who had come to the pool in jean cutoffs and a slightly too large The Who t-shirt (stolen from Dean) that hung effortlessly off his lithe muscular frame.

"You’ve got to be kidding me," Cas fought every urge to lick his boyfriend or straddle him right then and there. He worried his eyes were giving his stupefied state away. 

"Problem?" Dean’s eyes turned teasing, narrowing. 

"You come back here looking like some sort of Greek God with your little red shorts and your bronze skin and your hip bones," Cas puffed, flustered. "Where do you get off?"

"Hm. Where do I begin?" Dean’s fingers found Cas’ hips, pulling so he had to shuffle closer. He gave a very obvious once over that had the dark-haired boy turning pink; he raised his eyebrows. "My shirt?"

Cas’ brought his eyes to the floor, suddenly more interested in the frayed edges of his flip flop than anything else.

"Smells like you," he muttered. 

"Hey, hey," Dean brought a hand to his jaw and urged his eyes back to meet his own. "I love it." 

Dean pressed a gentle kiss to his exposed collar bone, humming into the skin just enough to pull a giggle from Cas’ lips. Dean fought back his own smile, interesting, he thought as his other hand tightened around his hip bone, fingers curling just a bit. 

"Uh oh," Dean watched the corners of Cas’ mouth twitch into a smile, then a frown, then a smile again. "You were hiding something from me?" His lower lip jutted out into a pout.

"It er," Cas coughed, his hand coming down to dislodge Dean’s tickly grip on his hip. "It never came up?"

"Hm. A month of coffee dates, hanging out, sleepovers,” his breath hummed into Cas’ ear, seductive and teasing.”You calling me ‘giggles’ and watching my sadistic co-workers in action and it never came up?”

"Hehe. I suppose not?"

Cas backed up half a step before Dean had him pinned against the back of the shed, mouth peppering soft and purposeful kisses all over his neck. He let out a steady stream of giggles and protests, cheeks turning a deeper shade of red with each second.

"Pleheheease, someone mihihght heeeheear or seheehee!" Cas squirmed, his hands landing on Dean’s chest, yelping again when his hands started to wander. "Please!"

"Well, you might not want to laugh so loud, darlin’. We have a lot of catching up to do," Dean growled, fingers finding the soft space between his hips and ribs, kneading away. 

Cas felt his nerves ignite, moving from the unpleasant wiggling that came from unwanted tickly kisses to the intolerable sparks in his nerves from a full-fledged tickle assault. Between half-closed eyes he could just make out the devious and unfairly adorable smile on his boyfriend’s face. Probably thankful to not be on the receiving end for once. 

"Hmm," Dean slowed his hands thoughtfully, giving Cas a chance to bring his breathing up to speed. He toyed with the hem of Cas’ t-shirt thoughtfully, dipping back in to bring their lips together in earnest. 

"Mhhm, this is better," Cas smiled into the kiss, thinking that he’d put up with anything, whatever Dean wanted, to keep this part up. "I like this."

Dean made quick work of the other man’s shirt, tossing it to the floor and cupping his now-bare hip. 

"Yeah?" Dean ran his hands back down Cas’ arms, linking their fingers together and easing them up over his head, pinning his arms to the shed. It was only when his hands were being held by one of Dean’s, as he was deepening the kiss and grinding his hips, that Cas realized what happened. 

"You sneaky— assbutt!" He cursed, sort of, as a hand scraped at his now exposed rib cage. 

"I’m a what-now?" Dean’s eyes crinkled with a smile at how adorable his now helpless boyfriend was as his nervously wriggled against his grip. 

"An ahahass-buhuhutt!" Cas choked on his laughter when Dean’s fingers teased along the bottom ribs, scratching at each bone in a torturous ascent. He stalled right beneath his underarm, noting a sharp intake of breath. 

"And you’re adorable," he dropped a kiss on Cas’ forehead before letting his hand fall into the sensitive area of his underarm. 

"Nohohohoho! PLEASE!" Cas eyes bugged out and his legs kicked a bit more in a more desperate attempt to squirm away. "Anywhere but there, ohohoho myhihiha Gohahahd!" 

"Nope. Just me, Dean. Close, though," he alternated between armpits at a maddening pace that had Cas shrinking into the wall of the shed, desperate to bring his severely weakened arms down.

"Cassie?" a small voice sounded making Dean pause. "De, what you do to Cassie?"

Dean turned around and made out a head of wet, golden hair. Gabriel toddled over and looked up at the two boys with curious eyes.

"I’m just ticklin’ him, Gabe," Dean released Cas’ hands, but made no move from his position blocking him into the wall. "Just playing a game is all."

"You like Cassie, right?" Gabe’s lip jutted out. "Mikey and Luke say’d they tickle me when i’m a’noidin’," he stopped to stage whisper, "Is Cassie a’noidin you?"

"It’s ‘annoying,’ Gabe," Cas smiled through deep breaths. "They said they did that when you were annoying. But they’re just meanies.”

"S’what I said," Gabe looked unimpressed at Cas’ corrections, toddling closer to the two boys.

"Yeah, squirt," Dean ruffled at the boy’s hair. "And Cas ain’t annoying at all. In fact, wanna hear a secret?" 

Dean’s voice suddenly took on a conspiratory tone, ducking to whisper something to the little boy who giggled gleefully. 

"You do?" Gabe’s chubby cheeks framed an over-sized baby tooth smile. Dean whispered something else. "You will?" 

"Cross my heart," Dean followed through with the gesture. "and I always keep my promises.”

Gabe nodded, looking back between the two older boys with a giddy smile.

"Now, you go put on your water wings and wait with your brothers and I’ll watch you on the diving board before I go back on duty," Dean stood up straighter. "That sound good?"

Gabriel let out an excited squeal before he speed walked around the corner, mindful of the “no running” rule, but chattered excitedly to himself the entire way. 

"What did you say to him?" Cas asked, face still a bit pink and hair stuck up in different directions. 

"Nothin’," Dean ducked in to whisper, mouth trailing near his ear. "Just said I like your smile… and that I plan to make you smile for a long time."

"Yours ain’t bad either," Cas left a chaste kiss on his boyfriend’s nose, grinning as his face scrunched. "Even if you’re an assbutt."

"Careful," Dean warned, picking up Cas’ discarded shirt and throwing it over one shoulder, his other hand reaching down to intertwine their fingers. "I still intend to find out every place you’re ticklish. I’ve got some catching up to do, after all.”

Cas gulped as the two reemerged from behind the shed. He had no doubt because Dean always kept his promises.


	2. Part II: Learning Curve

**Summary for the Chapter:**

> Dean always keeps his promises.

**Notes for the Chapter:**

> There’s tickling, blowjobs, teasing and references to young people fumbling their way through some kinkier stuff. The characters are both at least 18 though (it’s a college AU because writing HS age squicks me out as an adult lady person). If this ain’t your cup of tea, I suggest floating off into the Masterpost sunset for something fluffy and PG.
> 
> I like porn here as much as the next person but I like not making people uncomfortable a bit more. If you stop before the last like fourth you’ll also be fine, I think.

”Where did you even get these?” Cas giggled, albeit it a bit nervously, fingers running along the soft edge of the fuzzy handcuffs Dean had pulled from his bedside drawer. 

Both men had shed their shirts in an earlier heated make-out session, Dean’s belt was undone but still laced through his belt loops; Cas’ sweatpants hung low, haphazardly off his tanned hips. They’d taken a short “detour from debauchery,” as Cas so aptly put it (earning a sharp poke from Dean) to flip the record they were listening to — Cas’ favorite Coltrane album — and it eventually led to Cas laying on his stomach fiddling with the crowded bedside drawer and fingering through the weird collection of items Dean had almost forgot about.

"A friend thought it was a funny graduation present a while back," Dean’s face reddened as he pulled out his favorite Zeppelin album to queue up next. "Stupid joke about me becoming a stripper."

Cas hummed thoughtfully, shifting into a pretzel style position, looking up at Dean through hooded eyes.

"Care to give me a sample of your skills?" his eyebrow quirked, teasing, the cuff twirling along his long finger.

"I’m beyond your paygrade," Dean huffed, falling onto the bed alongside his boyfriend. 

"Mhm. I’m sure," Cas nodded solemnly, still twirling the cuffs. 

"You’ll poke someone’s eye out," Dean said gruffly, grabbing the smaller man’s wrist. "Quit it."

"Why don’t you make me," Cas’ pink tongue stuck out childishly, eyes hinting at the cuffs suggestively and Dean raised his eyebrows. 

"Hm. I haven’t thought about trying ‘em out before but —" he swung a leg over Cas’ and pushed his shoulders with just enough pressure for him to fall back with an "oof."

"Gimme," he made grabby hand for the cuffs, still around Cas’ fingers. The other man handed them over. "Hands up, baby."

"I hate that endearment," Cas’ face contorted a bit as he reached his arms up, sort of tensing when he felt the first click of the cuff and then the other after they looped through the headboard. 

"We’ll have to negotiate on the proper ‘endearments’ then, oh lover of mine, light of my life, fire of my loins, holder of my hear-" 

"Quit it you," Cas bucked his legs to knee Dean in the back. His cheeks were flushed pink. 

"uh uh uh," Dean wagged a finger. "I’d be nicer to me if I were you."

"Oh, yeah?" Cas eyes darkened a bit, kind of just realizing that he couldn’t touch Dean no matter how desperately he wanted to. And, fuck, he felt himself more aroused than he was already.

"Yeah," Dean leaned down and pressed his lips too softly against Cas’. Ghosting over the skin and just lingering. Cas inched his head forward to deepen it but Dean just pulled back, a smile on his face. "This will be fun."

Cas would deny to his dying day that he whined.

"Now, you have to be nice,” Cas tugged at his arms. “It’s not fair.”

"I’m pretty sure you being cuffed to the bed means we go my speed, darlin’," Dean’s drawl came out with that word near constantly and it was probably one of the few "endearments" Cas allowed with (minimal) complaint. He pouted regardless. "It was your idea."

"Don’t make me regret it," Cas flinched when Dean’s hands ran up his sides, nails blunt but lethal until they landed cradling his hips. 

"Mhm, I’m pretty sure I said I wanted to find out every place you were ticklish, ‘member that?" 

"No idea what you’re talking about," Cas tried to scrunch his legs to dislodge the other man but was only rewarded with a pinch to his hips that made him squirm. "Isn’t there something —- II don’t know —- more sexy we could be doing?”

"Hm. I’ve got an idea!" Dean pulled at his belt and Cas licked his lips. Only to frown when Dean crawled down to the end of the bed and lashed his ankles together before resuming his position. "You losing control, seeing that smile and hearing your adorable giggles? Ain’t nothing sexier than that."

He punctuated that by splaying his fingers over his rib cage, urging out a whimper of a giggle. 

"But if you don’t want to for real, just tell me," Dean’s eyes shifted from lust to concern instantly. "Like, uh, a safeword or whatever. It’s only sexy if you’re having fun."

"O-okay," Cas held in his breath as Dean’s fingers curled. He probably meant it to be a reassuring affectionate gesture but Cas flinched anyway, feeling hyper sensitive and exposed. "What should it be?"

"I don’t know. S’got to be something other than ‘stop’ or ‘fuck off’ since you curse like a sailor when I get you going," Dean grinned. "I’m an assbutt, if I remember correctly."

"You are," Cas muttered, earning a thumb jabbing into his side that he couldn’t evade. 

"What’s your word, angel?" Dean pressed, relaxing his fingers and feeling a bit of the tension leave the other man’s body.

"Let’s go with that," Cas shrugged. "Angel works."

"Sacrilegious," Dean nodded. "You are a kinky fucker."

"Says the man with the handcuffs." Cas rolled his eyes.

"Says the man who dared me to use them," Dean countered, walking his fingers over Cas’ exposed belly. "Again, my suggestion is to play nice."

Cas’ middle went a bit concave as he tried to hold his muscles in and away from Dean’s fingers.He was taking inventory of his limbs and realized how much he must trust Dean to let him go at his exposed body like this. 

"Don’t suck it in on me," Dean chastised, voice soft and syrupy, as he just rubbed his hand over the skin. Cas couldn’t stand the teasing, biting his lip and closing his eyes. "You’ve got a cute little belly."

"Fu-huck yo-hoo," Cas’ teeth gritted together when a finger tip drifted over his belly button. 

"Okay, so let me go over what I know," Dean continued to circle his finger over the dip of skin and Cas was already squirming at the maddening, seemingly unconscious touches. "Let me know if I miss anything?"

"Belly button," he swirled a bit faster and forced out a curse as Cas tried to hold back a laugh.

"Tummy…" he scribbled his fingers across the skin of his belly and Cas shook his head, throwing it back with a giggle-filled "no-ho-ho-ho." 

"Ribs are good," he wiggled over the skin as if he was playing an accordion, working fingers between each bone with enough to pressure to bring out some real belly laughs. "Aw, I think we opened the floodgates now."

Cas’ eyes shot open when he saw Dean’s hands inch up toward his underarms, both totally exposed in his current position and he tugged at his arms frantically, head shaking.

"Hahahaa way-hay-hay-t, not there, please, wait," Cas heaved out a heavy breath and Dean paused to take in his already wrecked appearance. His sex hair was wild and unkempt, cheeks pink and chest heaving and they’d barely started.

"Your armpits are bad, huh?" Dean paused, hovering above them with poised fingers.

"The w-worst," Cas bit his lip, eyeing the offending hands warily. 

"We’ll save them for later then." He faked a hand toward the sensitive area but instead ducked under his boyfriend’s neck, inspiring a peal of laughter. "What about your knees? You know getting his knees make Sammy cry." 

"Really, talking about your brother with your boyfriend cuffed to your bed?" Cas ribbed. "Talk about setting the moo—-Ohoohaha no!" 

Cas tried to bend his legs to protect the hyper sensitive areas under his knees, but Dean had one hand firmly on his thigh. When that hand pinched at the skin between the thighs, protected only by a thin pair of sweats, his laughter jumped up an octave. 

Cas really had only been tickled by his aunts and uncles or his older brother and sister but it had never been for long. He’d always been fast and squirmy enough to evade prolonged exposure (not for lack of trying on Alfie and Anna’s parts) and it’d always been a quick squeeze to the side or a scratch at his armpit if he left the area exposed. He knew he was sensitive but he had no idea his legs could be that bad. He yelped when Dean’s fingers trailed dangerously close to his suddenly very attentive cock. 

"If I didn’t know better, I’d say you were enjoying this, babe," Cas gasped when Dean’s fingers trailed over the hardened area, unable to control the way his hips bucked closer. He turned his face into his arm to hide his blush as best he could.

"Hey, hey, hey," Dean appeared, hands framing his cheek bones and brushing some fly away hairs from his face. "Whatever it is, I think I’m liking it too."

And Cas could see it —feel it too — through the worn denim. His pupils were wide, black nearly dwarfing the green and Cas just wanted to feel him. He took the break Dean was giving him to catch his breath and oh-so-subtly cant his hips toward Dean’s ass for some much needed friction. 

"Hey!" Dean’s lips curved into a smirk as he lifted his butt, moving instead to crouch just inches from Cas’ reach, to the vocal frustration of the latter. "Patience, young grasshopper."

Cas let out an honest-to-God growl of irritation. 

"I’ll make it worth your while, promise," Dean smoothed a hand over Cas’ stomach, sliding down to ghost over his cock again just to watch his face contort. "Hey?"

"What?" Cas groaned when the hand moved away again.

"Do you got ticklish feet?"

"I don’t know, actually," Cas wiggled his toes, remembering being little and having his mother tickle his feet before bedtime only to cringe at the complete lack of sex appeal that image had. "Maybe?"

"We’re going to find out!" Dean took a pillow that had been knocked to the floor and placed it over Cas’ bound shins, straddling his legs facing the tops of his bare feet. He took an experimental finger and slid it slowly down and back up his left foot. 

It might’ve been the sharp intake of breath, the way his legs seized up or how his toes curled up like a hedgehog on the defense, but either way, Dean knew he’d hit a bad spot. Maybe on par with the arm pits.

"Cas," he stroked again, this time harder, more purposeful. "If I can tickle your feet for, like, a minute straight without you laughing, I’ll stop there and give you the best blowjob of your life."

Cas held his breath. The deal sounded good and Dean could do unfairly devious things with his mouth; it made his cock twitch just thinking about it. 

"And if I," He bit back a sound from the back of his throat as a nail was introduced, spiraling around the sole. "can’t do that?"

"We try something else," Dean peaked back, eyes twinkling and evil.

"O-okay,’ Cas stuttered when he felt Dean’s thumb and forefinger wrap around his big toes, the skin there was also too sensitive for his liking. He lightly tugged the toes back and the rest of his foot followed, the skin taut. "W-what’s that for?"

"S’more tickly when you can’t scrunch your feet up," Dean gave him a goofy grin before brandishing his fingers in a claw shape over his head, clearly just to taunt Cas. 

Before Cas could reply, four fingers scraped and wiggled down the exposed skin zeroing in on the center of his arch, moving down, up, down, up at an unforgiving pace. Dean was going on a hunch, knowing his own feet wouldn’t stand a chance with such treatment and he was right. He started wiggling horizontal patterns under the ball of his foot, alternating between there and his surprisingly soft heels, and finally earned a yelp and a stream of laughter. It was definitely only forty seconds, at most. 

"Ooof, so close," Dean released his toes, first wiggling his fingers in between the area to get one more squeal from his boyfriend. "So, I guess it’s plan B."

"I think I’m—" Cas sucked in a gulp of air, "I think I’m going to hate plan B."

"Your arms doing okay? Nothing hurting?" Dean slowed down, hands running to stroke at Cas’ palms, smile quirking when even that seemed to tickle him. 

"Nothing ‘the best blowjob of my life’ couldn’t fix," Cas huffed, still painfully turned on and seeking some sort of relief.

"Alright, alright, the crowd has spoken," Dean straddled Cas, laying on top of him, hips pressed together. "You have one more thing you gotta do and it’s a one way ticket to deep throat city."

"You’re vulgar," Cas rolled his eyes, gasping at the well-timed roll of Dean’s hips. "And a monster."

"This last part is simple, though," Dean’s fingers walked up his ribs and Cas cursed under his breath. "Just gotta laugh for me."

Dean launched a ten finger assault on his underarms that had him yanking hard on his wrists, desperate to bring them down. As Dean alternated between spidering his fingers and driving his thumbs into the centers, Cas’ laughter shifted from the deep, if a little hoarse, belly laughter, to a silent sort. His head was thrown back, tears staining at his cheeks, when Dean slowed down a bit. He was gently stroking circles into the squirming man’s armpits, noticing how the more he squirmed the better it felt for his own aching cock. 

"Had enough?" Dean smiled, deceptively sweet, before moving in to kiss Cas deeply. 

"B-blow me," he heaved, his face red and hair matted by sweat.

"I can’t tell if that’s an order or an attempt at back talk," Dean shrugged, leaning down to remove his belt from Cas’ legs before tugging down his sweats and underwear in a fluid motion. 

"Sure you want this, baby?" Dean settled between his legs, hand grasping at his cock and offering a quick, wrist-flicking stroke. "You ready?"

"Don’t fucking tease, Dean," Cas groaned, bucking into his hand. "I want, I need, I…" he babbled.

"Tell me what you need, darlin’," Dean had seen Cas come apart before, but he never thought he would see him so desperate, after a half hour of tickling of all things. 

"Want you. Your mouth. Come on!" Cas dug his heels into the bed when he felt Dean’s breath along his skin. Dean tongued at his slit, sliding over the head and could feel his whole body shiver. "Please, Dean."

He took him into his mouth, the taste of Cas blocking every other sense as he worked, swiping his tongue and hollowing his cheeks in time with the man’s rhythm. 

Cas let out a whimper, tugging suddenly violently on the cuffs and making the bed creak and rattle. 

"What if I stopped here," Dean pulled back. "What would you do?"

"I would fucking kill you," Cas writhed, urging his hips forward to reclaim the warm and perfect feeling from seconds before. 

"Ask nicely," Dean grinned and Cas wanted to throttle him. 

"Please, baby, please," he rattled off as if speaking in tongues and Dean had to force away the smile at Cas’ use of one of his "awful endearments." He resumed his ministrations, even attempting to relax his throat (the way he’d seen porn stars do it) to take him in deeper.

"Oh God, I’m going to," Dean pulled off of him with a pop of his lips and Cas’ eyes rolled back, hips practically vibrating as he came, cuffs rattling against the headboard. Dean hummed softly, rubbing his stomach in the least tickly way he could as he rode it out. 

"You’re perfect," Cas sighed, sated, shifting his wrists. "Now, let me return the favor."

"You know, I actually heard people are more ticklish post orgasm," Dean said thoughfully, fingers hooking under his ribcage. "Care to investigate?"


End file.
